Development of Organic Transformations Based on the Controlled Lewis Acidity of Indium(III) Compounds
摘要:
Four types of synthetic applications of indium (III) salts as characteristic Lewis acids have been discussed. (1) Reductive functionalizations of carbonyl compounds were assisted by a catalytic amount of indium (III) halides, which achieved reductive chlorination and reductive Friedel-Crafts alkylation of aldehydes or ketones, moreover presented reductive allylation and reductive aldol reaction of esters. (2) Direct substitution of hydroxy groups of alcohols and carboxylic acids were also achieved by characteristic interactions between indium trihalide catalyst and silicon moieties. (3) Indium halides catalyzed direct couplings of alcohols with carbon nucleophiles such as enol acetates or 1,3-dicarbonyls were achieved. (4) A novel type of carboindation of alkynes or alkenes was successful, in which direct anti addition of indium tribromide and carbon nucleophiles to alkynes or alkenes takes place.
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DOI:
10.5059/yukigoseikyokaishi.72.1360
年份:
2014
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